A series of new Schiff bases of 4-(methylthio)benzaldehyde derivatives 3(a-i) were synthesized by the reaction of 4-(methylthio)benzaldehyde with various amines 2(a-i). Newly synthesized compounds were characterized by elemental analyses, UV-visible, FT-IR, Mass and 1H NMR spectral studies. All compounds were evaluated for their in vitro antibacterial activity against clinically isolated strains i.e., E. Coli, P. Fluorescence, M. Luteus and B. Subtilis. These compounds were screened for their antioxidant activity by 2,2-diphenyl-1-picryl-hydrazyl (DPPH•) and ferrous ion chelating assay (Fe2+) methods. The cytotoxicity assay was performed by tryphan blue dye exclusion method. Compounds 3g, 3h and 3i exhibited good antibacterial activity when compared with other compounds in the series against tested pathogenic bacterial strains. All the compounds showed antioxidant activity, where compound 3b was the best radical scavenger and Fe2+ ion scavenger. These findings showed that the Schiff bases of 4-(methylthio)benzaldehyde derivatives possess antioxidant activity with different mechanism of actions towards the different free radicals tested. Among these derivatives, 3b and 3h had the strongest activity against human peripheral lymphocytes.